


we're all sensitive people (with so much to give)

by strideofpride



Category: Gossip Girl (TV 2007)
Genre: Alternate Universe - Canon Divergence, Insecure Dan, Multi, discussion of sex obviously but nothing graphic, serena & vanessa are just an old married couple in this
Language: English
Status: Completed
Published: 2021-02-25
Updated: 2021-02-25
Packaged: 2021-03-16 15:14:57
Rating: Mature
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 1,162
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/29702499
Author URL: https://archiveofourown.org/users/strideofpride/pseuds/strideofpride
Summary: He briefly considers going to Nate for advice, before realizing it would be better to get a woman’s perspective on all of this. Or two women, really.Or, the one where Dan goes to Serena & Vanessa for advice on how to please Blair.
Relationships: Dan Humphrey & Serena van der Woodsen & Vanessa Abrams, Dan Humphrey/Blair Waldorf, Vanessa Abrams/Serena van der Woodsen
Comments: 6
Kudos: 21





	we're all sensitive people (with so much to give)

**Author's Note:**

> This idea popped into my head this morning and made me laugh so hard, I just had to write it. I'd say this fits in an AU of season 4 but it doesn't really matter.
> 
> Edited to add that this is probably obvious but this was based off that one episode of Friends where Monica & Rachel gave Chandler sex advice.

Dan wakes up with a text from Blair. _Looking forward to tonight ;)_

The gross part of Dan can’t help but think _finally_. They had been dating for over two months now, but she had wanted to take things slow, ease into their new relationship, not even letting him sneak a hand up her skirt. He had recently been spending quite a bit of his time taking cold showers.

The insecure part of Dan starts to panic though. In addition to the past two months of sexual frustration, Dan had been celibate for quite a while, pining after Blair. What if he can’t last very long? What if he makes a total fool of himself? What if he’s the worst sex of her life? He doesn’t want that; he wants it to be as great for her as he knows it will be for him.

He briefly considers going to Nate for advice, before realizing it would be better to get a woman’s perspective on all of this. Or two women, really.

He calls up Vanessa. “What do you want at this ungodly hour?” she answers groggily.

He pretends to be apologetic but he’s really not. “Hey, I’m sorry, is Serena there too?”

“Ugh, wake up, Dan wants to talk to you.”

Dan can hear Serena groan over the phone. “Does he realize how fucking early it is?”

“Yeah, I don’t think he cares.”

“Ugh, asshole.”

“I’m still here and I can hear both of you,” he says wryly. “Look, just come over to the loft for brunch, okay? We’ll talk then.”

\---

Vanessa and Serena come over a little after eleven, both still a little irritated with Dan for waking them up so early.

“Okay, what was _so_ important that you just _had_ to wake us up this morning?” Vanessa says as they all take a seat at the counter.

Dan rubs his hands together nervously. “Uh, it’s about Blair.”

“Oh, god, what did she do now?” Serena asks. “Or what did you do now?” She narrows her eyes at him.

“Nothing, nothing,” Dan assures her. “Everything’s fine. It’s just uh…Blair kinda implied this morning that tonight was the night that we finally…well, you know.”

“Oh, well, that’s great. You’ve been way too on edge,” Vanessa tells him.

“Yeah, get in there,” Serena jokes.

Vanessa shoots her a look. “Don’t do that, don’t be that person.” But she’s smiling fondly as she says it.

“So, what, you called us all the way over here to brag that you’re going to fuck Blair tonight?” Serena asks him.

“No, no. I was actually hoping you guys might have some advice on, uh…how to please her?” He feels his face start to heat up.

“Advice? What do you need our advice for? You’ve done it before,” Vanessa says.

“Yeah, Dan you were fine. No complaints from either one of us,” Serena adds.

“But I don’t want to be just fine. I - I just really want to please her.” He hangs his head down, embarrassed.

“Aw, that’s sweet,” Serena practically coos at him. “Just be in the moment, get out of your head. You love her so that’s going to make it perfect no matter what.”

Vanessa rolls her eyes. “Okay, mom. Dan, here’s how you make Blair come so hard she sees stars.” She proceeds to give him extremely explicit and precise tips on just that, while Serena chimes in now and then with what she knows Blair specifically likes. Eventually, Vanessa turns to Serena, annoyed. “Why do you know so much about Blair’s sexual preferences?”

“Oh my god, do _not_ be jealous. We’re best friends, we talk about all of that stuff. Didn’t you two?”

“God, no,” Dan and Vanessa say at the same time.

“Wait, what do you tell Blair about me?” Vanessa asks her.

“Uh…nothing,” Serena says, unconvincingly.

“Oh my god, you are such a liar!”

“Ladies, ladies, save the domestic dispute for later, back to my issue please.”

After another fifteen minutes of graphic instruction that makes Dan feel very grateful that he suggested they meet at the loft instead of a diner, Vanessa and Serena finally wrap up.

“Don’t worry about it too much though, Dan,” Vanessa tells him. “I’m sure Serena will have a full progress report from Blair she can share with you tomorrow.”

Serena throws her hands up in the air. “Oh my god, you gotta get over it!”

Dan smiles to himself, always glad to see two of his favorite people act like such an old married couple.

\---

On the way to the penthouse that night, Dan stops and buys the nicest bottle of wine fifty dollars can get him. He considers buying candles as well but knowing Blair she probably already had a hundred of them lining her room. He does pick up a bouquet of red roses though, too.

He’s nervous when he gets off the elevator and sees her already waiting for him on the couch. He hands her over the bottle and the flowers awkwardly. “Uh, these are for you.”

Blair raises an eyebrow. “What’s all this for?”

Dan shrugs. “I just wanted tonight to be special for you.”

She looks at him, confused. “Why, I’ve seen _Breakfast at Tiffany’s_ literally hundreds of times.”

He starts to feel like a real idiot. “Oh, I just thought…with your text…the winky face…never mind, let’s just watch the movie,” he says, a little disappointed but trying to hide it.

Blair won’t let him off the hook that easily though. “Oh my god, you thought we were going to have sex tonight, didn’t you?”

Dan shrugs again, embarrassed. “In my defense, that winky face was very misleading.”

She crosses her arms, looking a little upset. “I’m sorry that I’m not ready, okay? I know it’s been driving you crazy. And I want to eventually, I do. But after everything that happened last year, I just…I don’t want to screw this up, is all.”

Dan puts his hands on her shoulders, trying to be comforting. “Hey, hey, I’m sorry if I’m making you feel pressured. We don’t have to do anything tonight. We don’t have to do anything ever, if you want. My right hand might go permanently numb, but I’ll live.”

Blair shoots him a look, but then shakes her head. “No. Soon, okay? I promise.” She blushes a little bit as she says that. “But for now, can we just chastely watch the movie? Down here?”

Dan nods. “Of course.”

\---

Three weeks later, Dan basks in the afterglow with Blair, who finally catches her breath and looks over at him, surprised. “Where did you learn how to do _that_?”

Dan smirks. “Yeah, uh, I’m not quite sure you’re going to want to know the answer to that.” He tells her anyway though, and Blair puts her hands over her face.

“Oh god, I have to send Vanessa a thank you card, don’t I?” she groans. Dan just laughs.


End file.
